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Literature DB >> 22307724

An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Adam E Goetz¹, Sarah M Bronner, Jordan D Cisneros, Joshua M Melamed, Robert S Paton, K N Houk, Neil K Garg.

Abstract

Think before you act: a computational approach is reported for evaluating the synthetic potential of heterocyclic arynes. Routine and rapid calculations of arene dehydrogenation energies and aryne angle distortion predict the likelihood that a given hetaryne can be generated, as well as the degree of regioselectivity expected in a reaction between a given hetaryne and a nucleophilic trapping agent.

Entities: Chemical Gene

Mesh：

Substances：
Heterocyclic Compounds

Year: 2012 PMID： 22307724 PMCID： PMC4502420 DOI： 10.1002/anie.201108863

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

33 in total

1. Stereoinduction by distortional asymmetry.

Authors: Robert V Kolakowski; Lawrence J Williams
Journal: Nat Chem Date: 2010-02-28 Impact factor: 24.427

2. Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles.

Authors: Claude Y Legault; Yeimy Garcia; Craig A Merlic; K N Houk
Journal: J Am Chem Soc Date: 2007-10-03 Impact factor: 15.419

3. Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

Authors: Daniel H Ess; K N Houk
Journal: J Am Chem Soc Date: 2007-08-09 Impact factor: 15.419

4. Experimental investigation of the absolute enthalpies of formation of 2,3-, 2,4-, and 3,4-pyridynes.

Authors: Nathan J Rau; Paul G Wenthold
Journal: J Phys Chem A Date: 2011-08-26 Impact factor: 2.781

5. Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors: Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal: J Am Chem Soc Date: 2011-08-11 Impact factor: 15.419

6. Benzannulated bicycles by three-component aryne reactions.

Authors: Kevin M Allan; Christopher D Gilmore; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2011-04-11 Impact factor: 15.336

7. A five-step synthesis of (S)-macrostomine from (S)-nicotine.

Authors: Monica F Enamorado; Pauline W Ondachi; Daniel L Comins
Journal: Org Lett Date: 2010-10-15 Impact factor: 6.005

8. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors: G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2010-11-29 Impact factor: 15.419

9. Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring.

Authors: Toshiyuki Hamura; Yousuke Ibusuki; Kazuhiko Sato; Takashi Matsumoto; Yoshihiro Osamura; Keisuke Suzuki
Journal: Org Lett Date: 2003-10-02 Impact factor: 6.005

10. Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides.

Authors: Robert D Bach
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

15 in total

An efficient computational model to predict the synthetic utility of heterocyclic arynes.

1. Stereoinduction by distortional asymmetry.

2. Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles.

3. Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

4. Experimental investigation of the absolute enthalpies of formation of 2,3-, 2,4-, and 3,4-pyridynes.

5. Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

6. Benzannulated bicycles by three-component aryne reactions.

7. A five-step synthesis of (S)-macrostomine from (S)-nicotine.

8. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

9. Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring.

10. Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides.

1. Metallacycles: breaking the rules.

2. Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

3. Computational predictions of substituted benzyne and indolyne regioselectivities.

4. Quantification of the Electrophilicity of Benzyne and Related Intermediates.

5. Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.

6. Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

7. The Aza-hexadehydro-Diels-Alder Reaction.

8. Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

9. Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

10. Concise enantiospecific total synthesis of tubingensin A.